5-bromo-2-(4-methylphenyl)benzofuran | 22772-25-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-bromo-2-(4-methylphenyl)benzofuran
• 英文别名: 5-Bromo-2-(4-methylphenyl)-1-benzofuran
• CAS: 22772-25-4
• 化学式: C₁₅H₁₁BrO
• 分子量: 287.156
• InChiKey: UOMDGOUTYJZDAR-UHFFFAOYSA-N

物化性质

• 沸点：
  385.8±27.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(4-methylphenyl)benzofuran 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 反应 6.0h， 以63%的产率得到5-bromo-2-[4-(bromomethyl)phenyl]-1-benzofuran
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates

  摘要：

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.

  DOI：

  10.1016/0223-5234(93)90084-r
• 作为产物：
  描述：

  2-(4-Bromophenoxy)-1-(4-methylphenyl)ethanone 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 6.0h， 生成 5-bromo-2-(4-methylphenyl)benzofuran
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates

  摘要：

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.

  DOI：

  10.1016/0223-5234(93)90084-r

文献信息

• Pd-Catalyzed Tandem Chemoselective Synthesis of 2-Arylbenzofurans using Threefold Arylating Triarylbismuth Reagents
  作者：Maddali L. N. Rao、Deepak N. Jadhav、Priyabrata Dasgupta

  DOI：10.1002/ejoc.201201314

  日期：2013.2

  A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o-hydroxy-gem-(dibromovinyl)benzenes and BiAr3 reagents under palladium-catalyzed conditions. This unique and synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth reagents and provides 2-arylbenzofuran products in high yields.

  2-芳基苯并呋喃的串联化学选择性合成是在钯催化条件下由邻羟基宝石-(二溴乙烯基)苯和BiAr3试剂完成的。这种独特且具有合成价值的策略通过涉及三芳基铋试剂的三个连续偶联反应进行，并以高产率提供 2-芳基苯并呋喃产品。
• One-Pot Preparation of 2-Arylbenzofurans from Oximes with Diaryliodonium Triflate
  作者：Hideo Togo、Kotaro Miyagi、Katsuhiko Moriyama

  DOI：10.3987/com-14-13071

  日期：——

  A variety of 2-arylbenzofurans were obtained in good yields by the O-arylation of oximes with diaryliodonium triflates, followed by the treatment with HCl in dioxane under warming conditions through the [3,3]-sigmatropic reaction. The present reaction is one-pot transition metal-free method for the preparation of various 2-arylbenzofurans from oximes, which are easily available from the reaction of alkyl aryl ketones with hydroxylamine
• Palladium-catalyzed cross-couplings of functionalized 2-bromobenzofurans for atom-economic synthesis of 2-arylbenzofurans using triarylbismuth reagents
  作者：Maddali L.N. Rao、Dheeraj K. Awasthi、Jalindar B. Talode

  DOI：10.1016/j.tetlet.2012.03.059

  日期：2012.5

  The palladium catalyzed, atom-economic synthesis of various functionalized 2-arylbenzofurans was achieved through cross-coupling reaction of 2-bromobenzofurans with triarylbismuth reagents. The palladium catalytic protocol is very efficient to furnish various cross-coupled functionalized 2-arylbenzofurnas in high yields using triarylbismuth reagents with three aryl couplings as multi-coupling organometallic nucleophiles in one-pot operation. All the coupling reactions were completed in 1 h short reaction time involving three couplings from triarylbismuths under heating condition. (C) 2012 Elsevier Ltd. All rights reserved.